Pyridine → HCID 70605506, 화합물

HRID 614135

반응식

HRID 614135 반응식
[C:1]1([C:7]([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29](=O)[NH:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl[Si:49]([CH3:52])([CH3:51])[CH3:50].C(Cl)(Cl)=O.[N-:57]=[N+:58]=[N-:59].CN(C)C(=[NH2+])N(C)C.[OH-].[Na+]>O.C(Cl)(Cl)Cl>[C:1]1([C:7]([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29]4[N:30]([CH2:31][C:32]5[CH:37]=[CH:36][C:35]([O:38][Si:49]([CH3:52])([CH3:51])[CH3:50])=[CH:34][CH:33]=5)[N:59]=[N:58][N:57]=4)[C:25]([CH3:27])([CH3:28])[S:26][C@H:22]23)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

9

반응물 6

HCID 1049PyridineHCID 6371PhosgeneHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 70604879HCID 70604879, 화합물HCID 178484365HCID 178484365, 화합물

생성물 1

HCID 70605506HCID 70605506, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매2회

반응 조건

온도
4 °C

실험 절차

To a stirred solution of 1.69 g. (3 m mole) of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-hydroxybenzyl]carbamoyl)penam prepared as described in Example XIII in 9 ml. of chloroform is added 1 ml. (12 mmole) of pyridine. The solution is cooled to ca. 4° C. in an ice-bath and 0.80 ml. of chlorotrimethylsilane is added. The solution is stirred for 40 minutes at ambient temperature, and then it is again cooled to ca. 4° C. Phosgene (1.5 ml. of a 4.3 M solution in chloroform 6.45 mmole) is added and the cooling bath is removed. Stirring is continued for a further 1.5 hours, and then all the volatile components are removed by evaporation in vacuo. The oily residue is redissolved in 6 ml. of chloroform and the solution is cooled to ca. 4° C. in an ice-bath. To the stirred solution is added 0.95 g. (6 mmole) of tetramethylguanidinium azide, and then stirred is continued for a further 1 hour at ambient temperature. At this point, 25 ml. of water is added, followed by sufficient 1N sodium hydroxide to bring the pH of the aqueous phase to 10. The chloroform layer is removed, washed with water, dried using sodium sulfate, and evaporated to dryness in vacuo. This affords crude 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[4-trimethylsilyloxybenzyl]tetrazol-5-yl)penam, which is purified by chromatography on silica gel using chloroform as eluant.

후처리

  1. temperatureit is again cooled to ca. 4° C
  2. customthe cooling bath is removed
  3. stirringStirring
  4. waitis continued for a further 1.5 hours
  5. customall the volatile components are removed by evaporation in vacuo
  6. dissolutionThe oily residue is redissolved in 6 ml
  7. temperatureof chloroform and the solution is cooled to ca. 4° C. in an ice-bath
  8. additionTo the stirred solution is added 0.95 g
  9. waitis continued for a further 1 hour at ambient temperature
  10. customThe chloroform layer is removed
  11. washwashed with water
  12. customdried
  13. customevaporated to dryness in vacuo

출처 및 근거

ORD 기록
ord-1a5ad4fff2ac4543873c0da55fcd9fe1
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04143039

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